The perfect first sales enablement hire for an established B2B company
If you run an established B2B company, you probably have a sales team full of competent people.
You also have a museum.
Not the good kind with dinosaurs and gift shops, but the kind where customer conversations are built on stories that were born in 2011, polished in 2016, and last updated when someone’s “big innovation” was adding a new slide to the end of the deck.
And to be clear, this is not a dig at your reps. It is normal.
In established companies, selling is a craft that gets passed down. People learn what works, they keep doing it, they teach it to others, and it becomes muscle memory. Some of that muscle memory is pure gold. Some of it quietly costs you margin, focus, and consistency.
Because when every rep has their own history, you end up with 25 to 75 versions of your company in the market. Same logo, same products, same strategy deck, but different priorities in customer communication.
The real problem in established B2B sales
Most sales issues in mature companies are not about effort.
They are about everyone selling a slightly different company.
Ask five reps what you are best at, and you might get five believable answers. That is the problem. It means your customer’s experience depends on who happens to pick up the phone.
One rep leads with the legacy flagship product because it has always worked. Another leads with services because that is what they are comfortable explaining. A third jumps straight into features. A fourth goes deep on a niche use case because they once won a big deal with it in 2018 and it still feels like a cheat code. Meanwhile the company is trying to push a more profitable product line, a sharper message, or a new go to market focus, and it never fully shows up in customer conversations.
Content behaves the same way.
The newest deck is sitting in a folder somewhere, while the “trusted” deck from five years ago keeps getting emailed around because it feels safe and nobody wants to risk looking unprepared in front of a customer.
So the customer hears a story that might be true, but not necessarily the story you are trying to scale.
Multiply that across regions, segments, and experience levels, and you get a quiet tax on growth. Not dramatic enough to set off alarms, but steady enough to slow down execution of strategy year after year.
What the first sales enablement person is for
If your first enablement hire ends up running a training calendar you will be disappointed. You are not hiring a calendar manager.
You are hiring a force multiplier who makes the right customer conversation the default customer conversation.
In practical terms, the job is three things:
Create clarity. What is our identity, what is our message, what do we push, what do we stop pushing.
Make it easy. Build a simple system so reps can find, use, and trust the right story and the right assets without thinking.
Make it stick. Get adoption through frontline managers and the flow of work, not through one big launch event and a prayer.
This is not about controlling reps. It is about removing constant reinvention, and reducing the damage caused by everyone improvising a different version of the company.
The profile that actually works in an established org
The best first enablement hire is often someone who has lived in the field long enough to be instantly credible, but wants a different kind of impact now.
A common profile is a strong rep who used to be a top performer, but now only reaches 80 to 90 percent of their potential because the motivation to grind quota is fading. They are still sharp, still modern, still analytical, and you would hate to lose them. They are also not a natural sales director. They are an innovator and a coach.
They understand what sellers actually do on Tuesday at 14:20, when a customer asks a hard question and the rep has to respond right now.
That is the kind of credibility that makes change possible.
Traits to look for:
Trust with reps, they speak field reality without sounding like a consultant.
Builder mindset, they ship usable tools, not complex frameworks.
Coach energy, they improve behaviour without becoming the sales police.
Data literacy, they can tell the difference between a problem and a symptom.
Respect for legacy, they do not insult the veterans, they learn what works and keep it.
Courage to challenge legacy, they can say, “this story used to work, it now costs us margin.”
If you want a one line description, it is this.
A rep whisperer with operator DNA.
What they’ll deliver in the first 30, 60, 90 days
Established companies usually get this wrong by starting with a big launch.
New deck, new messaging, new training day, new enthusiasm, then two months later nothing has really changed because the old habits are easier than the new ones.
A better approach is simple. Map reality first, then build something small that sticks, then expand.
First 30 days, map the legacy
This is not about documenting the ideal sales process. It is about understanding the one that actually happens.
The work looks like this:
Talk to reps across experience levels, plus frontline managers.
Identify where reps improvise most, discovery, demo, proposal, pricing, negotiation.
Audit what reps actually use in deals, not what is “official”.
Find drift points, old content, wrong product focus, mixed messages.
Define a few non negotiables for identity and message, the things that must show up in every customer conversation.
This is also the trust phase. Lots of listening, lots of observing, and very little preaching.
Days 31 to 60, build a unified story that fits the process
Your sales process has phases, even if nobody has named them properly. Those phases are where customer communication happens, and that is where strategy either shows up or disappears.
The work looks like this:
Map the phases, keep it simple.
For each phase, define the job to be done, what needs to be true for the deal to move forward.
For each phase, define the core message, the proof points, and the focus products.
Create a content “golden path”, the easiest assets to find should be the right ones.
Archive outdated assets, or label them so nobody accidentally sells 2014.
This is where a company’s identity becomes real. Not as a brand deck, but as a consistent story that reps can actually use.
Days 61 to 90, drive adoption through managers and friction removal
Enablement only becomes a business function when adoption happens. Otherwise it becomes support, and support gets busy, and busy looks productive, and nothing changes.
The work looks like this:
Roll out through frontline managers, because managers create consistency.
Replace big launch theatre with weekly reinforcement.
Fix friction, naming, findability, what is current, what is outdated, what is approved.
Build a feedback loop so reps can improve the story without creating chaos.
Iterate fast, the first version should be usable, not perfect.
If reps are still freelancing the story after 90 days, it is usually not because reps are stubborn. It is because the right story is still harder to use than the old story.
What to measure so this does not become vibes
Enablement gets a bad reputation in some companies because it can feel like activities with no impact.
So measure behaviours and outcomes that reflect your real goal, consistency in customer communication and focus.
Weekly or monthly, track:
Product mix, are focus products showing up more often in real deals.
Usage of newest assets, not total usage, but current usage.
Stage conversion, especially where deals stall today.
Optional, discounting discipline, if margin is part of the problem.
You are not trying to prove enablement “did something”. You are trying to prove selling behaviour changed.
The biggest risks in established companies
Two failure modes show up again and again.
First, enablement becomes reactive. Random requests, deck updates, ad hoc trainings, “can you make a one pager”, and the drift continues.
Second, leadership does not enforce. Enablement becomes suggestions, suggestions become optional, optional becomes ignored.
Consistency requires air cover. Not control, just clear expectations.
The bottom line
Established companies do not need more sales activity.
They need more consistency in what happens when sales talks to customers.
The perfect first sales enablement hire is not there to make sellers more enthusiastic or to run more sessions. They make sure your company shows up as one company in the market, with a clear identity, a clear message, and a clear focus, even when 50 different people are doing the talking.
Because the easiest way to waste years of good strategy is letting every rep sell their own version of it.